Security

SentinelOne insiders sold $30.6 million in six months without buying a single share

The selling ran in the same weeks the company stacked $1.65 billion of new borrowing. Fiscal third-quarter results land on December 3, with the sellers on record.

Richard TangRichard Tangthree-minute read
Share
Tomer Weingarten, co-founder and chief executive of SentinelOne, in a dark suit and white shirt against a black background
1 / 6Slide 1 of 6
Tomer Weingarten, SentinelOne's co-founder and chief executive, booked ten sales worth an estimated $23 million in six months, most of the $30.6 million the company's six officers sold.

SentinelOne−0.63% — SentinelOne, down 0.63 percent today, the Mountain View cybersecurity company that sells itself as the leader in AI security 1, shows one pattern in its insider record: in the past six months of disclosed insider trades, every one was a sale. Insider-trading disclosures filed on Form 4 with the SEC show 34 open-market sales across the six officers named in them, and not one purchase 2. Together the officers booked an estimated $30.6 million, in the same weeks the company borrowed $1.65 billion that ranks ahead of the common stock 34.

Thirty-four sales, not one purchase

Chief executive Tomer Weingarten is most of it: ten sales worth an estimated $23 million, at prices averaging near $21.8 a share 2. That sits above the $20 median target across 14 analyst estimates 2; the chief executive has been selling above where analysts think the stock belongs.

The selling did not pause before the results

The run did not stop ahead of the earnings report: on November 10, chief accounting officer Robin Tomasello booked another $181,930 5. Several filings note the trades ran under Rule 10b5-1 plans, which fix a selling schedule in advance 2. A plan explains the calendar; nothing in the record explains the purchase that never came, from any of the six.

The CEO is most of six months of SentinelOne insider selling

Weingarten's $23.0M is most of the $30.6M six-officer total

$0M$5M$10M$15M$20M$25MWeingarten (CEO)$23MParekh (CFO)$3MConder (CLO)$1.4MTomasello (CAO)$1.2MPadgett (COO)$1.1MPinczuk (product)$1M
Data
Value
Weingarten (CEO)$23M
Parekh (CFO)$3M
Conder (CLO)$1.4M
Tomasello (CAO)$1.2M
Padgett (COO)$1.1M
Pinczuk (product)$1M
Estimated proceeds of open-market sales per officer, Form 4 filings, six months to November 10, 2026.2

The equity now sits behind $1.65 billion of paper

The borrowing came in two steps. October brought $1.25 billion of convertible notes paying no interest and maturing in 2031, priced while the company bought back $150 million of its own stock from the notes' buyers at $24.01 3. On November 12 came a $400 million revolving credit line from Bank of America, secured by substantially all company assets and undrawn at signing 4, which The Inference charted the next day. Both the notes and the credit line are debt: if the company ever liquidated, lenders and noteholders would be paid before common shareholders.

Growing, and still paying staff in stock

None of this describes a business in trouble. Last quarter revenue grew 21% to $292 million, annual recurring revenue rose 22% to $1.218 billion, and management raised its full-year outlook 6. But the company still lost $93 million in that quarter under standard accounting rules 6, and stock, the currency these officers are paid in, is what they keep converting to cash: in its last full fiscal year, stock compensation ran at roughly four times operating cash flow 7.

Stock pay has exceeded operating cash flow in all six years

  • Stock compensation
  • Operating cash flow
-$0.2B$0B$0.2B$0.4BFY2020FY2021FY2022FY2023FY2024FY2025Cash flow breakeven$0.3B
Data
Stock compensationOperating cash flow
FY2020$0.02B-$0.07B
FY2021$0.09B-$0.1B
FY2022$0.16B-$0.19B
FY2023$0.22B-$0.07B
FY2024$0.27B$0.03B
FY2025$0.3B$0.08B
Stock-based compensation and cash from operations in USD billions, by fiscal year ended January 31. In FY2025 stock pay was 3.9 times operating cash flow.9

No filing carries motive. What is on record is who sold, at what price, and how much.

Revenue has grown more than 20% year over year for ten straight quarters

The sellers are not reacting to a broken business

150M200M250M300MQ2 '24Q4 '24Q2 '25Q4 '25Q2 '26291.98M
Data
Revenue
Q1 '24186.36M
Q2 '24198.94M
Q3 '24210.65M
Q4 '24225.52M
Q1 '25229.03M
Q2 '25242.18M
Q3 '25258.91M
Q4 '25271.15M
Q1 '26276.66M
Q2 '26291.98M
Total revenue in USD millions per fiscal quarter, as labeled; year-over-year growth stayed above 20% in every quarter shown.8

December 3 arrives with the sellers on record

Results for the quarter ended October 31 arrive after the close on December 3, with a Barclays+0.13% — Barclays, up 0.13 percent today investor conference a week later 1. The shares fell 3.1% on November 12 as investors digested the filings 2. Anyone buying that dip is buying before the earnings report, with the sellers on record.

Not one of the 34 trades in six months was a purchase.

Get Security by email, free

The breaches, flaws and security vendors AI is putting to the test. In our daily email, every weekday.

Loading S

Reader comments

0 comments

    More in Security

    All in this topic →

    Security

    Lightspeed Venture Partners discloses its $1.2 billion Netskope stake with the stock above its average target

    Netskope closed Friday above the average analyst target on the day Morgan Stanley moved to the sidelines, and a filing with the SEC put Lightspeed Venture Partners' whole position on the record: 56.5 million shares, all in passive form. Anyone buying the stock into its December 2 results now knows exactly how much could come to market.

    Security

    Tether and Tron move their crypto crime unit from TRM Labs to Chainalysis; TRM launches a rival desk

    TRM Labs built the Tron-Tether crime-fighting unit, then watched the job go to rival Chainalysis; its same-day answer, Beacon Concierge, hands police a license-free path to freeze crypto at any issuer. The enforcement gap now reaches Circle (CRCL), whose USDC pitch rests on regulated reserves rather than seizure reach.

    Security

    CISA orders federal agencies to patch Check Point's exploited root-access flaw by Monday

    The November 16 deadline arrives with the first build that fixes both the root escalation and the PHP2Shell entry point, and with two end-of-support releases that get no fix at all. For Check Point investors the question is whether "a couple of dozen" compromised systems in one region is containment, or the visible edge of a base that partly cannot be patched.

    Security

    Okta's AgentCore deal with Amazon has no disclosed price, and its fiscal 2027 guide carries no agent revenue

    AWS's November 12 AgentCore update ships every session with its own identity, policy and audit trail, the same guarantee Okta sells, and Okta's filed fiscal 2027 guide carries no agent revenue. OKTA is up about 106 percent this year into a December 1 print that has to show the money.

    Security

    Palo Alto's Unit 42: Chinese attackers ran half of 25 autonomous AI hacks on Zhipu's GLM 5.2

    Unit 42's telemetry shows one operator used Zhipu's GLM 5.2 for 13 of 25 autonomous intrusions that reached a teachers' union and .mil and .gov accounts. The report hands Washington a named Chinese model as chip curbs gain votes, and lands on Z.ai's Hong Kong holders.

    Security

    SentinelOne signs $400 million credit line secured by substantially all its assets

    The five-year Bank of America line costs roughly $1.0 million to $1.4 million a year undrawn, and if it is ever drawn its lenders rank ahead of October's $1.25 billion of convertible noteholders in any claim on the company's assets. The next clue lands with earnings on December 3.

    Subscribe to TheInference for free